


Bottoming

by MoonlightIcarus



Series: Bobby Tries New Things [2]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Barebacking, Bobby Singer's House, Bottom Bobby Singer, Bottom Crowley (Supernatural), First Time Bottoming, M/M, Plot What Plot/Porn Without Plot, Size Difference, Size Kink, Smut, Top Crowley (Supernatural), hot bear on bear action
Language: English
Status: Completed
Published: 2019-10-06
Updated: 2019-10-06
Packaged: 2020-11-26 00:22:53
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,909
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20921099
Author URL: https://archiveofourown.org/users/MoonlightIcarus/pseuds/MoonlightIcarus
Summary: Bobby and Crowley have been dating for a while now. They both want to take a step toward sex but they have some roadblocks. Bobby doesn't want to bottom and Crowley didn't sell his soul for nothing. Crowley decides to takes one step back to take two steps forward.





	1. Bobby's Way

"So are we going to shag or just dance around each other?" Bobby almost spat his beer out with how frank Crowley was being. But he was also thankful he chose to do it in his house instead of in public.

"Don't we have a few things to discuss before we get that far," he was trying to use a diplomatic tone because he knew if he didn't his voice would be shaking.

"What's there to discuss? You drop you trousers and I bend you over and shove my cock up your nice arse." He was having fun being so vulgar and making Bobby blush a deep shade of red.

Trying desperately to regain his composer he muttered through his teeth, "Ain't gunna happen. Stuff doesn't go up there and even if it did your unnatural behemoth is not tearing me open." The words were having the wrong effect and were instead giving Crowley a very vivid image in his head.

"Love, you don't have to worry about that. I'm the King of Hell I could clean and stretch you right now and you'd be good to go." He walked behind the desk where Bobby was sitting and rested his hands on those eternally tense shoulders. He slowly started working his fingers into that tough skin. Applying extra pressure to make sure he could really feel it beneath his two shirts and a wifebeater.

Bobby wasn't easily persuaded by the massage. They'd masturbated in front of each other many times so he knew exactly how big the demon really was. The fucker was ten inches long and a lot more than an inch wide. He had the biggest dick on the planet which made sense cause he had to sell his soul for it. And it wasn't that he didn't find men attractive Bobby had sex with guys before, but he had always topped. His train of thought was interrupted by his own groan as Crowley worked his fingers into a particularly tough knot on his shoulder.

Crowley was all too aware of how stubborn Robert was and in a battle of wills either of them could win, however he had one goal in mind and he was more than willing to give a little to what he wanted in the end. "Why don't we try it both ways?" Crowley leaned down to Bobby's ear while still massaging his shoulders. "This time you can take me and next time we feel like it I'll be heading right up in there." They were both breathing hard just thinking about it.

The offer was so tempting. All he could think about was how long it had been since he had company that wasn't his own hand. And if he said yes he would only be agreeing to let Crowley fuck him once, so if he really couldn't stand it then there wouldn't be a second time around. Plus he wasn't in any danger. Crowley could solve any foreseeable problems with demon powers. 

"Deal but today I'm the one topping today." Those hands stilled for a moment and then resumed, moving up to the base of his neck to start working on the tendons there.

It was almost sad how easy it was for him to win out in the end. "Not a problem at all. Now did you want to do this now or later and would you like me to prep myself or let you do it the traditional way?" With each word his hands pressed in harder and his breathing became more ragged.

"Now." 

Taking a step back Crowley went beside the chair and looked him in the eyes. "So how do you want me?" Even if he was getting fucked he was going to be a cheeky little sod with a shit eating grin plastered from ear to ear.

Bobby stood up and pushed his chair out. "Over the desk." He pointed to the exact spot he had been earlier. "Lean over it and do what I say."

He did just that. Bending over the aforementioned desk at an angle that managed to nicely showed off his arse even in his suit. His upper body looming over the desk but not pressing against it as he leaned onto his forearms. He arched his back downward to present his arse even better and then spread his legs farther apart. "All done love."

Bobby knees hit the floor with a thud. They hurt but it was nothing too serious that he actually needed to worry about. He undid the belt buckle, button, and zipper then lowered the dress black dress pants and matching black briefs down to mid thigh. He moved ono the suit coat and dress shirt and shoved them up to the small of his back. Now he was greeted with a view of his prize. He could see the fine black hair lightly covering every inch of delicious skin and contrasting the pale white flesh wonderfully. It highlighted that nice big round ass Crowley had. His hands each took one cheek and squeezed, adoring how it had a nice giggle and give to it but managed to still have firm muscles underneath.

Spreading those cheeks he uttered his first command, "Prep your ass with you powers." He received a groan in response and then saw the slight change in that pucker in from of him. It looked shiny and slick and he noticed it wasn't clench quite like it was before. He then used Crowley's legs to help him stand back up.

He lowed his pants and underwear down to his thighs as well and lined up to push in. He got the head of his dick right up against it and without a warning pushed all the way into the base at once. They both moaned from the sudden change in stimuli. Bobby didn't even move at first. Just stood there taking it all in. That velvety heat encompassing him. The globes of that nice ass pressed against his pelvis. The way he had Crowley breathing heavily and how his whole torso shuttered with each breath. 

Deciding he'd spent enough time just standing there admiring it he moved one hand onto Crowley's shoulder and his other hand to tangle in the bunched up fabric on his back. He pulled out a little more than half way and was right back inside. After that he kept his thrusts mostly short and shallow, hating the feeling of leaving that wonderful heat. Crowley would let out an obscene groan every time Bobby's balls smacked right against his ass. 

Bobby tended to only huff his breath and let out short muffled grunts. That all changed the second he started hitting Crowley's prostate. The sounds Crowley made each time it was hit were like something out of old VHS porn. He was so entranced by the lewd sound that he ended up letting out his own noises in response. 

The entire time Crowley's dick received no attention besides the occasional bump against the desk. But even that was few and far between so it mostly was jistjostled as it dibbled precome onto the floor.

Eventually Bobby pushed in as deep as he could go and started to gyrate inside as he chased his own orgasm. While he was at it he let out a seemingly never ending stream of obscenities. Crowley chose to have mercy on the hunter and clenched down as hard as he could. His effort was rewarded with a groan that resonated through the house and the feeling of his redneck coming deep in his ass. 

Bobby continued his little movements through his orgasm to really milk it and when he was done he didn't even pull out. Instead he leaned his full weight forward onto Crowley, rested his head on his upper back, and moved his hands around his torso. 

Crowley moved his arms and let his body lay directly against the desk. He then cradled his head on one arm and moved the other to start stroking himself to get off. He took big long strokes and used the precome gathered at the head to lube himself up. The resulting squelched were deliciously obscene and he came shortly there after leaving a stream of white on the side of Bobby's desk. The man didn't even respond to the mess because he was too entranced by the feeling of his dick going soft while still surrounded by that nice heat.


	2. Crowley's Way

**Summary for the Chapter:**

> Crowley cashes in on his part of the deal and Bobby struggles to keep up.

He had just dried off after his morning shower with a towel around his hips when he stepped into the bedroom and saw Crowley standing there in a black bathrobe.

"My turn love." His voice sounded rough and ruined but Bobby could barely take it in as he was suddenly lying naked on his stomach in his own bed. The abrupt shift in location left him too confused to protest and Crowley took this moment to explain himself. "Its time to come through on the other end of that you fuck my arse I fuck your's deal." He had dropped the bathrobe leaving both of them naked and climbed onto the bad between Bobby's legs. He slowly spread those thighs apart as he continued. "So now I'm going to finger that ass open until I'm sure you can take all of me. And once that's finished I will enjoy sliding into that tight virgin hole of your's and take all the time I feel like to get off. Sound like a good plan?"

"Yes!" He just managed to choke it out through the heady haze he was already in just from the description.

"I'll get started then," he had spread those legs a good distance but he still needed to grasp that arse and pull it apart a little bit to get a good view of Bobby's hole. When he saw it he contemplated going in and starting this off with a rim job to really get the hunter wound up but what he had planned would already take long enough.

He pulled a bottle of lube out of nowhere and poured some on one finger. He then went and just moved it over that twitching hole. In this time Bobby had moved a pillow under himself and he had started to squeeze it tighter every time Crowley moved his finger too close to his hole.

"C-Crowley what if I-"

"Don't worry I already cleaned you out love. In fact I could prep you immediately but seeing as it's your first time I figured we should at least do this the traditional way." He just took away every possible excuse Bobby could think of and with that he started rubbing the lubed digit against that hole. And then without a warning he pushed in to the first knuckle.

"Uugh," he was shocked by the sudden intrusion. "How am I supposed to take the monster you call a dick when this already feels like too much." He hated sounding like a scared piece of shit but he was actually fucking worried about some real permanent damage. There was a reason humans didn't naturally get that big.

"Slowly, love. Very very slowly." With that he made his intentions of taking up the whole day quite clear.

He started to spin and slightly move that one knuckle. He never went any deeper just moved it around a bit. Once he heard Bobby's panted breath even out he moved in deeper to the second knuckle and the process repeated. It took over half an hour to get to one finger full at this languid pace and that was exactly the point of it all. To keep his Robert stimulated but unable to come until he was balls deep in that tight arse. He then moved onto the second finger and repeated the process. Just in to the first knuckle and then slowly going deeper and deeper. So far the best part was when he was scissoring him open with two fingers and Bobby's arms never seemed to stop clenching around that pillow..

By the time he had three fingers all the way in they'd been at it for over seventy five minutes. Bobby bad started to dose off soon after he started the third round but what he had planned next was sure to keep wide awake. He pulled his hand out and then brought both hands up to that arse. He positioned them with both index and middle fingers back to back. Then he pushed all four in as deep as they could go at once.

Bobby had open his eyes from the zero to sixty movement but it got even better once Crowley went and pulled his fingers apart leaving the hunter gaping open. His head was thrown back and he released a tremendous moan as Crowley blew into that opening. Moving his fingers back together and leaving them inside Crowley started to surveyed his handiwork. Robert had been sweating profusely from the treatment and it made all his hair across his body stick tightly to his skin. His skin had also taken on a nice sheen and he was enjoying the occasion quiver of his ass.

"Alright love I'm going to go in now."

"Augh!" That was the only response he received and it made him all the happier. He knew he would be ruining Robert for everyone else. No one had a cock like him and no one would be able to please Bobby like he could.

He put both hands on Bobby's sides directly above the love handles for better leverage. He placed the head of his cock right in front of that now stretched hole and pushed just the tip in. Just like everything else he had done he was going to draw this out for as long as he could. And the moans he was forcing out of his hunter were proof this was a brilliant idea.

He had gotten about halfway in when he noticed that Bobby was grinding his cock into the mattress. Crowley then stilled his movement. "Love could you please stop? I know you're ready to blow, but I can guarantee this will be better if you wait a bit longer." The tone he used seemed far too pleasant and genuine given the circumstances. He received an annoyed huff in response and as Bobby stopped his movements Crowley resumed his.

At nine inches deep he heard another protest. "Crowley...can't....no more." The moans in his speech really spoke more about his state than the words themselves did. So wanton and desperate that he was unable to stop those noises even if he wanted to 

"Can you please last just a bit little longer. There really isn't that much left anyways." While speaking he continued to move inside, hoping that his speech would be too distracting for Robert to notice the last inch slipping in. He received a slight nod right when he had made it to the base.

Here he was as the first creature to ever say he was balls deep in Robert Singer. He left himself inside both for himself to enjoy the pressure and for Robert to get acclimated to it. He then slowly pulled out all the way to the head and with the same lack of urgency went right back in. Taking note of the way his massive bollocks smacked against that arse.

This repeated this a few times and then Crowley moved to change position. He moved his legs to frame Robert's ass and thighs as well as lowering himself to let his front rest on Bobby's back with his head resting between those shoulders. Next he threaded his fingers through Robert's hair and pulled his head back slightly letting him whisper directly into a blushing red ear. Finally using his legs and torso to pull out completely and plow right back in much faster than anything they'd done previously. It required a great deal of dexterity that would leave him sore afterwards, but it was absolutely worth it.

With that he started his brutal pace of long full thrusts. Taking care to fully pull out each and every time. Amid the passionate fucking he decided to gloat about his conquest just a little. "You know Robert I'm doing more than just taking your virginity back here. I'm also ruining sex with anyone else forever." Robert let out a confused sounding groan. "See no one is as big as me so no one will be able to make you this full or reach this deep into you and they won't be able to pound you into the mattress quite like this." Each declaration was accompanied by a fiercely brutal thrust. "I know you've been on edge for far too long dear so why don't you let go now." That was all the encouragement Bobby got before letting loose, coming between his bed sheets and his stomach. In the after glow of his orgasm he could feel the way Crowley was emptying himself into his ass. 

When Crowley pulled out Bobby felt exposed and vulnerable like never before. "As much as I'd love to stick around unfortunately I've still got a long list of souls to torture. Make sure to clean yourself up." Crowley took the liberty of smacking Bobby's ass hard and with that Bobby was left alone, splayed out on his bed and feeling too happy about what just happened to him.


End file.
